Hydrochloric Acid → 1-methyl-6-(4-(pyridin-2-yl-methoxy)-3-(trifluoromethyl)phenyl)-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile

HRID 517964ノート

反応式

HRID 517964 の反応式
[NH2:1][C:2]1[C:3]([C:28]#[N:29])=[N:4][C:5]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)=[C:12]([C:24]([F:27])([F:26])[F:25])[CH:11]=2)=[CH:6][C:7]=1[NH:8][CH3:9].Cl.[N:31]([O-])=O.[Na+].C(OCC)(=O)C>CN1C(=O)CCC1.O>[CH3:9][N:8]1[C:7]2[CH:6]=[C:5]([C:10]3[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=4)=[C:12]([C:24]([F:27])([F:26])[F:25])[CH:11]=3)[N:4]=[C:3]([C:28]#[N:29])[C:2]=2[N:1]=[N:31]1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 23668193Sodium NitriteHCID 672942713-Amino-4-(methylamino)-6-(4-(pyridin-2-ylmethoxy)-3-(trifluoromethyl)phenyl)picolinonitrile

生成物 1

HCID 533300421-methyl-6-(4-(pyridin-2-yl-methoxy)-3-(trifluoromethyl)phenyl)-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile収率 27.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
7.5 °C

実験手順

To 3-amino-4-(methylamino)-6-(4-(pyridin-2-ylmethoxy)-3-(trifluoromethyl)-phenyl)picolinonitrile (1.7 g) in NMP (20 ml) was added 1M hydrochloric acid (22 ml) and cooled to 5-10° C. with an ice bath. To above solution was then added dropwise a solution of sodium nitrite (0.59 g) in water (5 ml) during 5 minutes. The mixture was stirred at room temperature for another 1 hour. After adding ethyl acetate (200 ml), the mixture washed with water (4×100 ml), brine (50 ml), solvent removed under reduced pressure. Upon addition of methanol (20 ml) to the residue, the desired product precipitated and collected by filtration to give 1-methyl-6-(4-(pyridin-2-yl-methoxy)-3-(trifluoromethyl)phenyl)-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile (480 mg) as a white solid. 1H NMR (CDCl3) δ: 8.61 (d, 1H), 8.35 (s, 1H), 8.29 (d, 1H), 7.98 (s, 1H), 7.78 (t, 1H), 7.60 (d, 1H), 7.27 (t, 1H), 7.22 (d, 1H), 5.40 (s, 2H), 4.44 (s, 3H). MS m/z 411 (M+H).

後処理

  1. washthe mixture washed with water (4×100 ml), brine (50 ml), solvent
  2. customremoved under reduced pressure
  3. additionUpon addition of methanol (20 ml) to the residue
  4. customthe desired product precipitated
  5. filtrationcollected by filtration

出典と根拠

ORDレコード
ord-f23fecf460d04d538e062e3fc125d312
出典データセット
uspto-grants-2015_08
特許番号
US09115126B2

反応ノート

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